[5] He was born to a Jewish family in Williamsburg, Brooklyn, and grew up in the Bronx, the son of Max and Mae Simon.

[6] In 1981, Simon married Diane Meyer, political staffer for Senator Birch Bayh of Indiana.

[6] In 2002, Simon married Porntip Bui Nakhirunkanok (born February 7, 1969, Bangkok, Thailand), Miss Universe 1988.

[7][8] In 1983, Simon and his brother, Mel (1927–2009), purchased the NBA's Indiana Pacers from Sam Nassi and Frank Mariani.

[9][10] His nephew David (Mel's son) and he are also the owners of the WNBA's Indiana Fever[11] and formerly owned the USL's now defunct Reno 1868 FC.